TWI253460B - Curable organopolysiloxane composition, use of the cured product of the composition, and semiconductor device - Google Patents
Curable organopolysiloxane composition, use of the cured product of the composition, and semiconductor device Download PDFInfo
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
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- H01L2224/4809—Loop shape
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- H—ELECTRICITY
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/481—Disposition
- H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
- H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
- H01L2224/48245—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic
- H01L2224/48247—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic connecting the wire to a bond pad of the item
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
- H01L2224/85—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a wire connector
- H01L2224/85909—Post-treatment of the connector or wire bonding area
- H01L2224/8592—Applying permanent coating, e.g. protective coating
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/11—Device type
- H01L2924/13—Discrete devices, e.g. 3 terminal devices
- H01L2924/1301—Thyristor
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
- H01L2924/181—Encapsulation
Abstract
Description
1253460 五 、發明説明（ 曼明領域 本發明係關於一種可固化有機聚矽氧烷組合物及半導體 裝置。特而言之，本發明係關於一種可形成高光學穿透率 之固化產物及顯現較少隨時間而產生之熱誘導黃化之可固 化有機聚矽氧烷組合物，及關於一種高可靠度之半導體裝 置’其中’半導體元件係封裝於該組合物之固化產物中。 先前技藝 可固化有機聚石夕氧院組合物係做為光學半導體裝置（例 如光耦合器、發光二極體、固態影像拾取元件等）中半導體 元件之保護塗佈劑。當半導體元件發射或接收光線時，該 半導體元件之保護塗佈劑必須既不吸收亦不散射光線。 然而，當組合物係包含一種每個分子具有至少二個與矽 鍵結之烯基基團之有機聚矽氧烷、一種每個分子具有至少 二個與矽鍵結之氫原子之有機聚矽氧烷、及一種鉑金屬錯 合物，且該組合物之固化產物受熱超過延長時間後，該固 化產物傾向於隨時間黃化且固化產物的光學穿透率也會下 降。特而言之，具有封裝於該固化產物之半導體元件之半 導體裝置的可靠度已傾向降低。 因此，本發明之目的即在於提供一種可固化之有機聚矽 氧烷組合物，其可形成具有優越光學穿透率之固化產物， 並顯現較少隨時間而產生之熱誘導黃化、及一種高可靠度 之半導體裝置，其中，半導體元件係封裝於該組合物之固 化產物中。 發明概要 本發明之可固化之有機聚矽氧烷組合物係包含至少（a) -4- 本纸張尺度適用中國國家標準(CNS) Μ規格χ 297公爱） 1253460BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a curable organopolyoxane composition and a semiconductor device. In particular, the present invention relates to a cured product which can form a high optical transmittance and exhibits A heat-induced yellowing curable organopolyoxane composition produced over time, and with respect to a highly reliable semiconductor device in which a semiconductor component is encapsulated in a cured product of the composition. The organic polyoxo composition is used as a protective coating agent for a semiconductor element in an optical semiconductor device (for example, an optical coupler, a light-emitting diode, a solid-state image pickup element, etc.). When a semiconductor element emits or receives light, the The protective coating agent for the semiconductor element must neither absorb nor scatter light. However, when the composition comprises an organopolyoxane having at least two fluorene-bonded alkenyl groups per molecule, one for each An organopolysiloxane having at least two hydrogen atoms bonded to a ruthenium, and a platinum metal complex, and the composition is cured After the heat is heated for an extended period of time, the cured product tends to yellow with time and the optical transmittance of the cured product also decreases. In particular, the reliability of the semiconductor device having the semiconductor element encapsulated in the cured product tends to decrease. Accordingly, it is an object of the present invention to provide a curable organopolyoxane composition which forms a cured product having superior optical transmittance and exhibits less thermally induced yellowing over time, and A highly reliable semiconductor device in which a semiconductor component is encapsulated in a cured product of the composition. SUMMARY OF THE INVENTION The curable organopolyoxane composition of the present invention comprises at least (a) -4- paper The scale applies to the Chinese National Standard (CNS) ΜSpecification χ 297 public) 1253460
一種每分子具有至少二個與矽鍵結之烯基基團及具有與石夕 鍵結之芳基基團之有機聚矽氧烷，（B) 一種每分子具有至少 二個與矽鍵結之氫原子之有機聚矽氧烷，及（c) 一種鉑之有 機石夕氧烷寡聚物錯合物。該可固化之有機聚矽氧烷組合物 之特徵在於相對於在該成分（A)中之所有與石夕鍵結之有機 基團，在該成分（A)中與矽鍵結之芳基基團之含量不少於4〇 莫耳％，及在該成分（C)之有機矽氧烷寡聚物中，每分子具 有不多於8個矽原子且具有與矽鍵結之烯基基團及與矽鍵 結之芳基基團。 本發明之半導體裝置之特徵在於裝置中的半導體元件係 封裝於上述可固化有機聚矽氧烷之固化產物中。 圖式簡簟說明 圖1係光耦合器之剖示圖，其係作為本發明之半導體裝置 之實施例。 圖2係發光二極體之剖示圖，其係作為本發明之半導體裝 置之實施例。 1 ·半導體元件 2. 導線架 3. 打線 4. 半導體元件 5. 導線架 6. 打線 7·可固化有機聚矽氧烷組合物之固化產物 8. 密封樹脂 9. 半導體元件 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐)An organopolyoxyalkylene having at least two fluorene-bonded alkenyl groups per molecule and having an aryl group bonded to the ruthenium, (B) one having at least two bonds bonded to the molecule An organopolyoxyalkylene of a hydrogen atom, and (c) an organic rhomboster oligo complex of platinum. The curable organopolyoxane composition is characterized by an aryl group bonded to the oxime in the component (A) with respect to all of the organic groups bonded to the stagnation in the component (A). The content of the group is not less than 4% by mole, and in the organic siloxane oxide oligomer of the component (C), there are not more than 8 germanium atoms per molecule and have an alkenyl group bonded to the oxime. And an aryl group bonded to a hydrazine. The semiconductor device of the present invention is characterized in that the semiconductor element in the device is encapsulated in the cured product of the above curable organopolyoxane. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a cross-sectional view of an optical coupler as an embodiment of a semiconductor device of the present invention. Fig. 2 is a cross-sectional view of a light-emitting diode as an embodiment of the semiconductor device of the present invention. 1 ·Semiconductor component 2. Conductor frame 3. Wire bonding 4. Semiconductor component 5. Conductor frame 6. Wire bonding 7· Curing product of curable organopolyoxane composition 8. Sealing resin 9. Semiconductor component This paper scale applies to China Standard (CNS) A4 size (210 X 297 mm)
線 1253460 A7 _ B7 五、發明説明（3~) 10. 導線架 11. 導線架 12. 打線 13·可固化有機聚石夕氧烧組合物之固化產物 14.透明密封樹脂 發明詳細說明 首先解釋本發明之可固化有機聚石夕氧烧組合物。成分 (A)(本發明組合物之主要成分）係一種每分子具有至少二 個與石夕鍵結之烯基基團且具有與矽鍵結之芳基基團之有機 聚矽氧烷。烯基基團係例如乙烯基、烯丙基、丁烯基、戊 烯基及己烯基。此外，芳基基團係例如苯基、甲苯基、二 甲苯基及莕甲醯基。再者，與矽鍵結之有機基團（除了烯基 基團及芳基基團）係例如經取代或未經取代之單價烴類基 團，例如甲基、乙基、丙基、丁基、戊基、己基、庚基及 其它烷基基團；苯甲基、苯乙基及其它芳烷基基團；氣甲 基、3-氣丙基、3, 3, 3-三氟丙基及其它鹵化烷基基團。由 於本發明之組合物係假設由於光的反射、折射及散射等僅 引起很少之光衰減，因此本發明之組合物之特徵在於相對 於在成分（A)中之所有與矽鍵結之有機基團，其係含有不少 於40莫耳％(較佳地係不少於45莫耳％)之與矽鍵結之芳基基 團。此外，成分（A)之分子結構係例如直鏈、部分分支之直 鏈、分支、環狀及網狀結構。雖然沒有特別限制成分（A)之 黏度，但其在25°C之黏度係較佳地在10至1，000,000毫帕斯 卡-秒（1^31)之範圍，且更佳地係在1〇〇至50,〇〇〇111?3.3之 範圍。當黏度小於上述範圍之下限時，藉由固化本發明 -6- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 1253460 A7 _________ B7 五、發明説明（4 ) 之組合物而獲得之固化產物的機械強度將傾向於降低。另 一方面’當含量超過上述範圍之上限時，本發明之組合物 之操作特性將傾向於劣化。 成分（B)(作為本發明之組合物之固化劑）係一種每分子 具有至少二個與矽鍵結之氫原子之有機聚矽氧烷。在成分 (B)中與矽鍵結之有機基團係例如經取代或未經取代之單 價烴類基團，例如甲基、乙基、丙基、丁基、戊基、己基 庚基及其匕燒基基團；苯基、甲苯基、二甲苯基、萘甲 醯基及其它芳基基團，·苯〒基、苯乙基及其它芳烷基基團 :氯甲基、3_氣丙基、3,3,3-三氟丙基及其它鹵化烷基基 團。此外’成分（B)之分子結構係例如直鍵、部分分支之直 鏈、分支、環狀及網狀結構。雖然沒有特別限制成分之 黏度’其在25°C之黏度係較佳地在〇·ι至1，〇〇〇,〇〇〇〇〇〇 mPa.s之範圍〇 只要含量足以使本發明之組合物固化，則關於本發明之 組合物中之成分（B)之含量沒有限制。例如，對於成分（A) 之有機聚矽氧烷所含之每個與矽鍵結之烯基基團而言，其 含量較佳為使得在該成分及其他作為可視需要之成份之有 機石夕化合物中之與矽鍵結之氫原子數目係在〇1至1〇個原 子之範圍，較佳係使得原子數目在〇·1至5的範圍，更佳係 使得原子數目在〇·5至5的範圍。當成分（Β)的含量低於上述 範圍之下限時，則本發明之組合物將傾向於完全無法固化 。另一方面’當其超過上述範圍之上限時，則藉由固化本 發明之組合物而獲得之固化產物的物理性質傾向於降低。 成分（C )係用以促進本發明之組合物之固化之催化劑，其 -7- 本纸浪尺度適用中s s家標準(CNS) Α4規格(21()X2974D —- 1253460Line 1253460 A7 _ B7 V. Description of the invention (3~) 10. Conductor frame 11. Lead frame 12. Wire-bonding 13· Curable product of curable organic polyoxo-oxygen composition 14. Transparent sealing resin Detailed description of the invention First explain this The curable organic polyoxo-oxygen composition of the invention. The component (A) (the main component of the composition of the present invention) is an organic polyoxyalkylene having at least two alkenyl groups bonded to the group and having an aryl group bonded to the oxime. Alkenyl groups are, for example, vinyl, allyl, butenyl, pentenyl and hexenyl. Further, the aryl group is, for example, a phenyl group, a tolyl group, a xylylene group and a fluorenyl group. Further, the organic group bonded to the oxime (except for the alkenyl group and the aryl group) is, for example, a substituted or unsubstituted monovalent hydrocarbon group such as a methyl group, an ethyl group, a propyl group or a butyl group. , pentyl, hexyl, heptyl and other alkyl groups; benzyl, phenethyl and other aralkyl groups; gas methyl, 3-vapor propyl, 3, 3, 3-trifluoropropyl And other halogenated alkyl groups. Since the composition of the present invention assumes that only a small amount of light attenuation is caused by reflection, refraction, scattering, and the like of light, the composition of the present invention is characterized by organically bonded to all of the bonds in the component (A). The group which contains not less than 40 mol% (preferably not less than 45 mol%) of a fluorene-bonded aryl group. Further, the molecular structure of the component (A) is, for example, a linear, partially branched linear, branched, cyclic, and network structure. Although the viscosity of the component (A) is not particularly limited, the viscosity at 25 ° C is preferably in the range of 10 to 1,000,000 mPas-sec (1^31), and more preferably 1 〇〇. To 50, 〇〇〇111?3.3 range. When the viscosity is less than the lower limit of the above range, the composition of the invention is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) by curing the -6-sheet scale of the present invention. 1253460 A7 _________ B7 5. Composition of the invention (4) The mechanical strength of the cured product obtained will tend to decrease. On the other hand, when the content exceeds the upper limit of the above range, the operational characteristics of the composition of the present invention tend to deteriorate. The component (B) (as a curing agent for the composition of the present invention) is an organopolyoxane having at least two hydrogen atoms bonded to the oxime per molecule. The organic group bonded to the oxime in the component (B) is, for example, a substituted or unsubstituted monovalent hydrocarbon group such as methyl, ethyl, propyl, butyl, pentyl, hexylheptyl and An alkyl group; a phenyl group, a tolyl group, a xylyl group, a naphthylmethyl group, and other aryl groups, a benzoyl group, a phenethyl group, and other aralkyl groups: chloromethyl, 3_gas Propyl, 3,3,3-trifluoropropyl and other halogenated alkyl groups. Further, the molecular structure of the component (B) is, for example, a linear bond, a partial branched linear chain, a branched chain, a cyclic structure, and a network structure. Although the viscosity of the component is not particularly limited, its viscosity at 25 ° C is preferably in the range of 〇·ι to 1, 〇〇〇, 〇〇〇〇〇〇mPa.s, as long as the content is sufficient to make the combination of the present invention The content of the component (B) in the composition of the present invention is not limited as it is cured. For example, for each of the fluorene-bonded alkenyl groups contained in the organopolyoxane of component (A), the content thereof is preferably such that the component and other components as a component of the visual need The number of hydrogen atoms bonded to the ruthenium in the compound is in the range of 〇1 to 1〇, preferably such that the number of atoms is in the range of 〇·1 to 5, and more preferably the number of atoms is 〇·5 to 5 The scope. When the content of the component (Β) is less than the lower limit of the above range, the composition of the present invention will tend to be completely incurable. On the other hand, when it exceeds the upper limit of the above range, the physical properties of the cured product obtained by curing the composition of the present invention tend to be lowered. Ingredient (C) is a catalyst for promoting the curing of the composition of the present invention, and -7- the paper wave scale is applicable to the s s standard (CNS) Α 4 specification (21 () X2974D - 1253460
為一種具有有機石夕氧烧寡聚物配位基之始錯合物配位美 係具有與矽鍵結之烯基基團及與矽鍵結之芳基基團，且在 每個在分子中之鉑原子具有不多於8個矽原子。成分（(：）之 有機矽氧烷寡聚物較佳為由下列通式表示之有機♦氧燒寡 聚物：a coordinating group having an organic oxo-oxygen oligomer ligand having a aryl group bonded to an anthracene group bonded to a hydrazine and an aryl group bonded to a hydrazine, and each in a molecule The platinum atom has no more than 8 germanium atoms. The organic siloxane oxide oligomer of the component ((:) is preferably an organic oxime oxy-oligomer represented by the following formula:
R——si——RR——si——R
R 1 R—S-R 在該通式中，R代表相同或不相同之單價烴類基團，例如 甲基、乙基、丙基、丁基、戊基、己基、庚基及其它烧基 ;乙嫦基、烯丙基、丁稀基、戊晞基、己婦基及其它埽基 基團，苯基、甲苯基、二甲苯基、莕甲醯基及其它芳基基 團；苯甲基、苯乙基及其它芳烷基基團；以及氯甲基、3一 氯丙基、3, 3, 3-三氟丙基及其它鹵化烷基基團，且至少一 個R係上述烯基基團之一及至少一個R係上述芳基基團之一 。此外，該通式之下標m係介於0至6之整數。有機矽氧烷寡 聚物係特佳地具有在分子鏈末端之烯基基團。該有機矽氧 烧募聚物係由下列通式表示： R2 /R2R 1 R—SR In the formula, R represents the same or different monovalent hydrocarbon group, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl and other alkyl groups; Mercapto, allyl, butyryl, pentamidine, hexyl and other sulfhydryl groups, phenyl, tolyl, xylyl, indenyl and other aryl groups; benzyl, Phenylethyl and other aralkyl groups; and chloromethyl, 3-chloropropyl, 3,3,3-trifluoropropyl and other halogenated alkyl groups, and at least one R is an alkene group as described above One and at least one R is one of the above aryl groups. Further, the subscript m of the formula is an integer from 0 to 6. The organooxane oligomer preferably has an alkenyl group at the end of the molecular chain. The organic oxime calcining polymer is represented by the following formula: R2 / R2
R1—S 卜 0‘Si-〇-一孕一R R2 8- 本紙張尺度適用中國國家標準(CNS) A4規格(210 χ 297公釐) 1253460 A7 B7 五、發明説明（6 ) 在以上通式中’R代表烤基基團（例如與上述相同之基團） 。R2係相同或不相同之單價烴類基團（例如與上述相同之基 團），且至少一個R2為上述基團中之芳基。上式之下標m係介 0至6之整數。1，3-二甲基-1，3-二苯基-1，3二乙烯基二矽氧 烷係一較佳之有機矽氧烷寡聚物。 成分（C)之主要成分係鉑及與其聯結之有機矽氧烷寡聚 物；然而，此外亦可包含上述之有機矽氧烷寡聚物及/或未 與鉑聯結之有機聚矽氧烷。有機矽氧烷寡聚物可為與上述 相同之有機石夕氧烧寡聚物，或是分子鏈之二末端均以二甲 基乙烯基矽烷氧基基團封阻之二甲基矽氧烧寡聚物、分子 鏈之二末端均以三甲基矽烷氧基基團封阻之二甲基矽氧烷 寡聚物等。此外，有機聚矽氧烷可為與上述使用於成分（A) 中相同之有機聚石夕氧燒，或是分子鏈之二末端均以二甲基 乙烯基矽烷氧基基團封阻之二甲基聚矽氧烷、分子鏈之二 末端均以三甲基矽烷氧基基團封阻之二甲基聚矽氧烷、分 子鏈之二末端均以三甲基矽烷氧基基團封阻之甲基苯基矽 氧烷與一甲基聚矽氧烷之共聚物等。再者，成分（c)係較佳 地具有低含量之氣；特而言之，其包含不超過1莫耳的氣， 更佳地，每莫耳鉑不超過〇· 01莫耳氯。 只要含量足以促進本發明之組合物之固化反應，則關於 本發明之組合物中之成分（(:）之含量沒有限制。例如，較佳 係使用可提供（以重量計）相對於本發明之組合物之0· 01至 1，000百萬分之一（ppm)的鉑之量。這是由於當成分（c)的含 量少於上述範圍之下限時，則本發明之組合物傾向完全無 法固化。另一方面，當成分（c)的含量超過上限時則並未 -9-R1—S 卜 0′Si-〇-一孕一 R R2 8- This paper scale applies to China National Standard (CNS) A4 specification (210 297 297 mm) 1253460 A7 B7 V. Description of invention (6) Above formula Wherein 'R represents a baking group (for example, the same group as described above). R2 is a monovalent hydrocarbon group which is the same or different (e.g., the same group as described above), and at least one R2 is an aryl group in the above group. In the above formula, the standard m is an integer from 0 to 6. 1,3-Dimethyl-1,3-diphenyl-1,3 divinyldioxane is a preferred organic oxane oligo. The main component of the component (C) is platinum and an organic siloxane oxide oligomer bonded thereto; however, it may further comprise the above-mentioned organic siloxane oligopolymer and/or an organopolyoxane which is not bonded to platinum. The organooxane oligomer may be the same organic anthraquinone oligo oligomer as described above, or a dimethyloxoxime which is blocked by a dimethylvinyl alkoxy group at both ends of the molecular chain. A dimethyl methoxy olefin oligomer or the like in which both ends of the molecular chain and the molecular chain are blocked by a trimethyl decyloxy group. Further, the organopolyoxane may be the same as the above-mentioned organic polyoxo-oxygen used in the component (A), or the two ends of the molecular chain may be blocked by a dimethylvinyl alkoxy group. Methyl polyoxane, a dimethyl polyoxane blocked by a trimethyl decyloxy group at both ends of the molecular chain, and both ends of the molecular chain are blocked by a trimethyl decyloxy group. a copolymer of methylphenyl siloxane and monomethyl polyoxane. Further, component (c) preferably has a low content of gas; in particular, it contains no more than 1 mole of gas, and more preferably, no more than 〇·1 mole chlorine per mole of platinum. The content of the component ((:) in the composition of the present invention is not limited as long as the content is sufficient to promote the curing reaction of the composition of the present invention. For example, it is preferred to provide (by weight) relative to the present invention. The amount of platinum in the composition of from 0.01 to 1,000 parts per million (ppm). This is because when the content of the component (c) is less than the lower limit of the above range, the composition of the present invention tends to be completely impossible. Curing. On the other hand, when the content of component (c) exceeds the upper limit, it is not -9-
1253460 A7 -_____ Β7 五、發明説明（7 ) 明顯地促進固化反應，而這是在經濟上不利的。 本發明組合物可包含做為可視需要之成分之3-甲基-1-丁快-3-醇、3, 5-二甲基—1 —戊炔—3-醇、苯基丁炔醇及其它 炔醇；3—甲基一 3 一戊烯基-1-炔、3, 5-二甲基-3_己烯基-卜 炔及其它烯炔化合物；1357—四甲基—1357—四乙烯基 環四石夕氧烧、1，3, 5, 7-四甲基-13, 5, 7-四己基環四矽氧烷 、苯基二氮嗤及其它反應抑制劑。雖然關於反應抑制劑之 含量沒有限制，但較佳地，每1〇〇重量份之成分（A)，其含 量應在0.0001至5重量份的範圍内。 此外’本發明之組合物可包含用以促進其黏著性之黏著 供應劑。該黏著供應劑係較佳地每分子具有至少一個與矽 鍵結之烷氧基基團之有機矽化合物。烷氧基基團係例如甲 氧基、乙氧基、丙氧基、丁氧基及甲氧乙氧基，而甲氧基 基團係最佳的。再者，除了與矽鍵結之烷氧基基團之外， 在有機矽化合物中之基團係例如甲基、乙基、丙基、丁基 、戍基、己基、庚基及其它烷基基團；乙烯基、烯丙基、 丁烯基、戊烯基、己烯基及其它烯基基團；苯基、甲苯基 、二甲苯基、莕甲醯基及其它芳基基團；苯甲基、苯乙基 及其匕芳烧基基團；鹵化烷基基團，例如氣甲基、3一氯丙 基、3, 3, 3-三氟丙基及其它經取代或未經取代之單價基團 ’ 3-縮水甘油氧基丙基、4_縮水甘油氧基丁基及其它縮水 甘油氧基烷基基團；環氧基環己基烷基基團，例如2-(3, 4一 環氧基環己基）乙基及3-(3, 4環氧基環己基）丙基；環氧烷 基基團，例如4-環氧丁基及8 —環氧辛基、及其它含有環氧 基之單價有機基團；3-(甲基丙烯羰氧基）丙基及其它含有 -10- 各紙張尺度適财s时標準(CNS) M規格( χ 297公董) --1253460 A7 -_____ Β7 V. Description of invention (7) Significantly promotes the curing reaction, which is economically disadvantageous. The composition of the present invention may comprise 3-methyl-1-butan-3-ol, 3,5-dimethyl-1-pentyne-3-ol, phenylbutynol and optionally as components Other acetylenic alcohols; 3-methyl-1,3-pentenyl-1-yne, 3,5-dimethyl-3-hexenyl-propyne and other enyne compounds; 1357-tetramethyl-1357-four Vinyl ring tetradoxime, 1,3,5,7-tetramethyl-13, 5,7-tetrahexylcyclotetraoxane, phenyldiazepine and other reaction inhibitors. Although the content of the reaction inhibitor is not limited, it is preferably contained in an amount of from 0.0001 to 5 parts by weight per 1 part by weight of the component (A). Further, the composition of the present invention may contain an adhesive supply for promoting its adhesion. The adhesive supply is preferably an organic ruthenium compound having at least one alkoxy group bonded to ruthenium per molecule. The alkoxy group is, for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a methoxyethoxy group, and the methoxy group is most preferred. Further, in addition to the alkoxy group bonded to the oxime, the group in the organic ruthenium compound is, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a decyl group, a hexyl group, a heptyl group, and other alkyl groups. a group; a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, and other alkenyl groups; a phenyl group, a tolyl group, a xylyl group, a fluorenyl group, and other aryl groups; a methyl group, a phenethyl group, and a fluorenyl group; a halogenated alkyl group such as a gas methyl group, a 3-chloropropyl group, a 3, 3, 3-trifluoropropyl group, and other substituted or unsubstituted The monovalent group '3-glycidoxypropyl, 4-glycidoxybutyl and other glycidoxyalkyl groups; an epoxycyclohexylalkyl group, for example 2-(3, 4 Monoepoxycyclohexyl)ethyl and 3-(3,4-epoxycyclohexyl)propyl; epoxyalkyl groups such as 4-epoxybutyl and 8-epoxyoctyl, and others Monovalent organic group of epoxy group; 3-(methacrylocarbonyloxy)propyl group and other products containing -10- each paper scale GS standard (CNS) M specification ( χ 297 DON)
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▲ 1253460 A7 B7 五、發明説明（8 ) 丙烯酸之單價有機基團；及氫原子。較佳地’有機石夕化合 物應具有可與成分（A)或成分（B)反應之基團。較佳地’有 機矽化合物係具有與矽鍵結之烯基基團或與石夕鍵結之氮原 子。再者，由提供相關於各式基板材質之優越黏著性之觀 點為之，有機梦化合物應較佳具有每分子至少一個含有玉衣 氧基之有機基團。該有機石夕化合物例如石夕炫化合物或石夕氧 烷化合物。矽氧烷之分子結構係例如直鏈、部分分支直鍵 、分支、環狀及網狀結構’而直鍵、分支及網狀結構係特 別較佳者。該有機石夕化合物例如3 —縮水甘油氧基丙基三甲 氧基矽烷、2-（3, 4-環氧基環己基）乙基三甲氧基石夕烧、3一 (甲基丙稀幾氧基）丙基三甲氧基石夕烧及其它石夕烧化合物’ 碎氧炫化合物（每分子具有至少一個與石夕鍵結之稀基基團 或與矽鍵結之氫原子及一個與矽鍵結之烧氧基基團）、梦氧 烷化合物或矽烷化合物（具有至少一個與♦鍵結之烧氧基 基團）與矽氧烷化合物（分別具有至少一個與石夕鍵結之經基 及一個與矽鍵結之烯基基團之）之混合物、由下式表示之矽 氧烷化合物： {(CH2=CH)CH3Si〇2/2}a(CH3〇i/2)b{CH2-CHCH2〇(CH2)3Si〇3/2}c \ / 〇 其中下標a、b及c係正整數，而矽氧烷化合物係由下式表 示： i(CH2=CH)CH3Si〇2/2}a(CH3〇1/2)b{CH2-CHCH2〇(CH2)3Si〇3/2}c{(CH3)2Si〇2/2}d u \ / 〇 -11- 本紙張尺度適^國®家標準(CNS) A4規格(210X297公釐)▲ 1253460 A7 B7 V. Description of the invention (8) Monovalent organic groups of acrylic acid; and hydrogen atoms. Preferably, the 'organic stone compound' should have a group reactive with the component (A) or the component (B). Preferably, the organic compound has an alkenyl group bonded to a hydrazine or a nitrogen atom bonded to a stellate. Further, the organic dream compound should preferably have at least one organic group containing a decyloxy group per molecule, from the viewpoint of providing superior adhesion to various substrate materials. The organic stone compound is, for example, a Shi Xi Xuan compound or a oxalate compound. The molecular structure of the oxane is, for example, a straight chain, a partially branched direct bond, a branched, a cyclic, and a network structure, and a direct bond, a branch, and a network structure are particularly preferred. The organic compound is, for example, 3-glycidoxypropyltrimethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxyxanthine, 3-monomethylpropaneoxy ) propyl trimethoxy sulphur and other smoldering compounds' sulphurous oxygen compounds (each molecule has at least one dilute group bonded to the ruthenium or a hydrogen atom bonded to ruthenium and a bond with ruthenium) An alkoxy group), a monoxane compound or a decane compound (having at least one alkoxy group bonded to ♦) and a oxoxane compound (having at least one vial and a pair of a mixture of a fluorene-bonded alkenyl group, a oxoxane compound represented by the formula: {(CH2=CH)CH3Si〇2/2}a(CH3〇i/2)b{CH2-CHCH2〇( CH2)3Si〇3/2}c \ / 〇 where subscripts a, b and c are positive integers, and the oxane compound is represented by the formula: i(CH2=CH)CH3Si〇2/2}a(CH3 〇1/2)b{CH2-CHCH2〇(CH2)3Si〇3/2}c{(CH3)2Si〇2/2}du \ / 〇-11- This paper size is suitable for the National Standard (CNS) A4 size (210X297 mm)
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1253460 A7 _ B7 五、發明説明（10 ) 固化而言，最佳為加熱）時發生。加熱之溫度係較佳地在5〇 至200 °C之範圍内。藉由這種方式固化本發明之組合物而獲 得之固化產物係似樹脂的、似凝膠的或似橡膠的，而特佳 地係似凝膠的或似橡膠的。 本發明半導體裝置之特徵在於裝置中的半導體元件係封 裝於上述可固化有機聚石夕烧組合物之固化產物中。半導體 元件係例如用在混合積體電路（ICs)及單石積體電路中之 半導體元件、固態影像拾取元件、閘流體、電晶體及二極 體。此外，半導體裝置係例如二極體、發光二極體、電晶 體、閘流體、光耦合器、電荷耦合裝置（CCDs)、單石ICs、 混合ICs、LSI (大型積體電路）及VLSI(超大型積體電路）裝 置。 圖1係顯示光耦合器之剖示圖，其係作為本發明裝置之實 施例。在圖1所示之光耦合器中，含有化合物半導體之半導 體元件（1)係黏晶至導線架（2 )，且進一步以打線（3)打線接 合於其上。此外，光接收半導體元件（4)係黏晶至面對半導 體元件（1)之導線架（5)，且進一步以打線（6)打線接合至該 導線架。半導體元件間的空隙係以可固化有機聚矽氧烷組 合物之固化產物（7)充填。再者，封裝於固化產物（7)之半 導體元件係以密封樹脂（8 )密封。 圖1所示之光耦合器的製造方法係包含將半導體元件 黏晶至導線架（2)，然後使用金屬打線（3)將半導體元件（1) 及另一導線架（2)(未顯示）打線接合。同樣地，光接收半導 體元件（4)係黏晶至面對半導體元件（1)之導線架（5 )，然後 使用金屬打線（6)將半導體元件（4)及另一導線架（5)(未顯 -13 - 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐)1253460 A7 _ B7 V. Inventive Note (10) In the case of curing, the best is heating). The temperature of the heating is preferably in the range of 5 Torr to 200 °C. The cured product obtained by curing the composition of the present invention in this manner is resin-like, gel-like or rubber-like, and particularly preferably gel-like or rubber-like. The semiconductor device of the present invention is characterized in that the semiconductor element in the device is encapsulated in a cured product of the above-mentioned curable organic polyceramic composition. The semiconductor element is, for example, a semiconductor element, a solid-state image pickup element, a thyristor, a transistor, and a diode used in a hybrid integrated circuit (ICs) and a monolithic integrated circuit. Further, semiconductor devices are, for example, diodes, light-emitting diodes, transistors, thyristors, optical couplers, charge coupled devices (CCDs), single-stone ICs, hybrid ICs, LSI (large integrated circuits), and VLSI (super) Large integrated circuit) device. BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a cross-sectional view showing an optical coupler as an embodiment of the apparatus of the present invention. In the optical coupler shown in Fig. 1, a semiconductor element (1) containing a compound semiconductor is bonded to a lead frame (2), and is further bonded thereto by wire bonding (3). Further, the light-receiving semiconductor element (4) is bonded to the lead frame (5) facing the semiconductor element (1), and is further wire-bonded to the lead frame by wire bonding (6). The voids between the semiconductor elements are filled with the cured product (7) of the curable organopolyoxane composition. Further, the semiconductor element encapsulated in the cured product (7) is sealed with a sealing resin (8). The manufacturing method of the optical coupler shown in FIG. 1 includes bonding a semiconductor element to a lead frame (2), and then using a metal wire (3) to bond the semiconductor element (1) and another lead frame (2) (not shown). Wire bonding. Similarly, the light-receiving semiconductor element (4) is bonded to the lead frame (5) facing the semiconductor element (1), and then the metal element (4) and the other lead frame (5) are used using the metal wiring (6) ( Not Displayed - 13 - The paper size applies to the Chinese National Standard (CNS) A4 specification (210 X 297 mm)
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Ϊ253460 A7 _ B7 五、發明説明（13 ) 如圖1所示之光耦合器係採用下列方式製造。即將GaA1As 化合物半導體元件（1)以導電膠黏晶至導線架（2)，然後使 用金屬打線（3)將半導體元件（1)與導線架（2)(未顯示）打 線接合。光接收器半導體元件（4)係以導電膠黏晶至半導體 元件（1)對面之導線架（5)，然後使用金屬打線（6)將半導體 元件（4)與另一導線架（5)(未顯示）打線接合。在以可固化 有機聚石夕氧烧組合物充填半導體元件間之空隙後，藉由將 其放置於150°C熱空氣循環烘箱中加熱1小時使其固化。接 著’封裝於可固化有機聚矽氧烷組合物之固化產物（7)中的 半導體元件係以白色環氧樹脂（8)密封。十個光耦合器係採 用上述方式製造。 光耦合器在放置於150t熱空氣循環烘箱中加熱ι〇〇小時 前後之發射輸出之量測結果係將熱處理前之發射輸出設為 100%，而顯示熱處理後之發射輸出之相對平均值。 i算半導體裝1可靠度之方法（方法9、 圖2所示之發光二極體係以下列方式製造。即將GaN化合 物半導體元件（9)以導電膠黏晶至導線架（iq)之後，使用打 線（12)將半導體元件（9)及導線架（11)打線接合^接著，在 以可固化有機聚矽氧烷組合物塗佈半導體元件（9)之後，藉 由將其放置於150°C熱空氣循環烘箱中加小時而使其固 化。然後’封裝於可固化有機聚石夕氧院組合物之固化產物 (13)之半導體元件（9)係以透明環氧樹脂（14)密封。十個發 光二極體係採用上述方法製造。 發光二極體之發射輸出係在將其放置於15〇熱空氣循 環洪相中熱處理1 0 0小時之則及之後而量測，並顯示為熱處 -16- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) ' --- 1253460 A7Ϊ 253460 A7 _ B7 V. Description of Invention (13) The optical coupler shown in Fig. 1 is manufactured in the following manner. That is, the GaA1As compound semiconductor element (1) is bonded to the lead frame (2) with a conductive paste, and then the semiconductor element (1) is wire-bonded to the lead frame (2) (not shown) using a metal wire (3). The photoreceptor semiconductor component (4) is made of a conductive adhesive to the lead frame (5) opposite to the semiconductor component (1), and then the metal component (4) is used to bond the semiconductor component (4) to the other leadframe (5) ( Not shown) Wire bonding. After filling the gap between the semiconductor elements with the curable organic polyoxo solder composition, it was cured by placing it in a hot air circulating oven at 150 ° C for 1 hour. Next, the semiconductor element encapsulated in the cured product (7) of the curable organopolyoxane composition is sealed with a white epoxy resin (8). Ten optical couplers were fabricated in the manner described above. The measurement results of the emission output of the photocoupler before and after being heated in a 150 t hot air circulating oven were set to 100% before the heat treatment, and the relative average of the emission outputs after the heat treatment was shown. i method of calculating the reliability of the semiconductor package 1 (method 9, the light-emitting diode system shown in Fig. 2 is manufactured in the following manner. That is, after the GaN compound semiconductor element (9) is made of a conductive adhesive crystal to the lead frame (iq), the wiring is used. (12) Wire-bonding the semiconductor element (9) and the lead frame (11). Then, after coating the semiconductor element (9) with the curable organopolyoxane composition, it is placed at 150 ° C by heat. The air circulating oven was allowed to cure for an additional hour. Then the semiconductor component (9) encapsulated in the cured product (13) of the curable organopolysilicate composition was sealed with a transparent epoxy resin (14). The light-emitting diode system is manufactured by the above method. The emission output of the light-emitting diode is measured after being placed in a 15 〇 hot air circulation flood phase for heat treatment for 10 hours and thereafter, and is shown as a heat--16- The paper scale applies to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) ' --- 1253460 A7
理後之發射輸出之相對值的平均 輸出為100%而計算。 參考實例1 其係以熱處理前之發射 以5(TC加熱400公克（g)1，3_二甲基_13二苯基一13-二 乙烯基二矽氧烷’並以滴落方式加入55g之氣鉑酸水溶液 (銘金屬含量=13重量％) ’並在7(rc授拌混合物i小時。然後 ’將混合物冷卻至室溫並加人55g碳氫化納及9g氣化妈。授 拌混合物之後，以過濾除去所產生之鹽後，即產生鉑錯合 物（I)，其係包含鉑之1，3-二甲基_13_二苯基_13_二乙烯 基二矽氧烷錯合物之1，3-二甲基_13一二苯基_13_二乙烯 基二矽氧烷溶液。 參考實例2 除了使用1，3-二乙烯基四甲基二矽氧烷代替參考實例i 中之1，3-—甲基_1，3 - 一苯基-1，3-二乙婦基二石夕氧烧以外 ，鉑錯合物（II)之製備方法係與參考實例1相同，其係包含 鉑之1，3-二乙烯基四甲基二矽氧烷錯合物之丨，3 —二乙烯基 四甲基二矽氧烷溶液。 應用實例1 黏度為10，000 mPa·s之可固化有機聚夕氧院組合物係經 由均勻混合100重量份做為成分（A)之甲基苯基聚石夕氧烧、 2· 5重量份做為成份（B)之甲基氫聚矽氧烷、做為成份（(：）之 始錯合物（I)、及0.05重量份做為反應抑制劑之3 -苯基一 1 一 炔基_3-醇而製備，其中，甲基苯基聚矽烷之黏度為12, 〇〇〇 mPa.s，且分子鏈之二末端以二甲基乙烯基矽烷氧基基團封 阻（與石夕鍵結之乙稀基基團含量= 0·20重量％，與石夕鍵結之笨 -17- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐)The average output of the relative value of the transmitted output is calculated as 100%. Reference Example 1 This was carried out by heat-emitting before 5 (TC heating 400 g (g) 1,3-dimethyl-13 diphenyl-13-divinyldioxane' and added 55 g in a drip manner. Aqueous platinum acid solution (Ming metal content = 13% by weight) 'And at 7 (rc mixing mixture for 1 hour. Then 'cool the mixture to room temperature and add 55g of sodium carbonate and 9g of gasification mother. Mixing mixture Thereafter, after removal of the salt produced by filtration, a platinum complex (I) is produced, which is a platinum-containing 1,3-dimethyl-13-diphenyl-13-divinyldioxane. a solution of 1,3-dimethyl-13-diphenyl-13-divinyldioxane. Reference Example 2 In addition to using 1,3-divinyltetramethyldioxane instead of the reference example The preparation method of the platinum complex (II) is the same as that of Reference Example 1 except that 1,3-methyl-1,3-phenyl-1,3-diethoxylate is used in i. It is a solution of platinum, 1,3-divinyltetramethyldioxane complex, and a solution of 3-divinyltetramethyldioxane. Application Example 1 Viscosity is 10,000 mPa· s curable organic polyoxo group The composition is obtained by uniformly mixing 100 parts by weight of methylphenyl polyoxoxime as component (A) and 2.5 parts by weight of methylhydropolysiloxane as component (B). (:) The starting complex (I), and 0.05 parts by weight of 3-phenyl-1-alkynyl-3-ol as a reaction inhibitor, wherein the viscosity of the methylphenyl polydecane is 12 , 〇〇〇mPa.s, and the two ends of the molecular chain are blocked by a dimethylvinyl alkoxy group (the content of the ethylene group with the Shi Xi bond = 0·20% by weight, with Shi Xi Bonding stupid-17- This paper scale applies to China National Standard (CNS) A4 specification (210 X 297 mm)
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!253460!253460
發射輸出之相對估 算值U)(方法2) 1業利用性 100 100 98 97 93 本發明之可固化有機聚矽氧烷組合物之特徵在於其可形 成具有高光穿透率且顯現較少隨時間而產生之熱誘導黃^ 之固化產物。本發明之組合物可用做電子或電子零件之黏 著劑、澆注劑、保護塗佈劑或底部灌充劑，且由於固化產 物固化之後並不會出現黃化，其特別適合做為光電半導體 元件之底部灌充劑、保護塗佈劑、澆注劑及黏著劑。此外 ，由於半導體元件係以本發明組合物之固化產物封裝，因 此本發明半導體裝置之特徵在於優越之可靠度。 -21 -Relative Estimation of Emission Output U) (Method 2) 1 Industry Utility 100 100 98 97 93 The curable organopolyoxane composition of the present invention is characterized in that it can be formed to have high light transmittance and exhibit less time with time. The resulting heat induces a cured product of yellow. The composition of the present invention can be used as an adhesive for an electronic or electronic component, a potting agent, a protective coating agent or a bottom filler, and is particularly suitable as an optoelectronic semiconductor component since the cured product does not appear yellow after curing. Bottom filling, protective coating, casting and adhesive. Further, since the semiconductor element is encapsulated with the cured product of the composition of the present invention, the semiconductor device of the present invention is characterized by superior reliability. -twenty one -
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| JP4040858B2 (en) | 2001-10-19 | 2008-01-30 | 東レ・ダウコーニング株式会社 | Curable organopolysiloxane composition and semiconductor device |
-
2001
- 2001-10-19 JP JP2001322138A patent/JP4040858B2/en not_active Expired - Fee Related
-
2002
- 2002-10-09 DE DE60223832T patent/DE60223832T2/en not_active Expired - Lifetime
- 2002-10-09 KR KR1020047005795A patent/KR100909575B1/en active IP Right Grant
- 2002-10-09 EP EP02802006A patent/EP1442081B1/en not_active Expired - Lifetime
- 2002-10-09 US US10/492,569 patent/US7271232B2/en not_active Expired - Fee Related
- 2002-10-09 WO PCT/JP2002/010499 patent/WO2003035763A1/en active IP Right Grant
- 2002-10-11 TW TW091123453A patent/TWI253460B/en not_active IP Right Cessation
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2007
- 2007-08-02 US US11/832,984 patent/US7763697B2/en active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI398488B (en) * | 2006-08-25 | 2013-06-11 | Dow Corning Toray Co Ltd | Curable organopolysiloxane composition and semiconductor device |
| TWI495688B (en) * | 2008-09-05 | 2015-08-11 | Dow Corning Toray Co Ltd | Curable organopolysiloxane composition, optical semiconductor element sealant, and optical semiconductor device |
| TWI462954B (en) * | 2008-12-05 | 2014-12-01 | Shinetsu Chemical Co | An addition-hardening type silicone compound having a high refractive index, and an optical component sealing material made of the composition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1442081A1 (en) | 2004-08-04 |
| US7763697B2 (en) | 2010-07-27 |
| KR20040048423A (en) | 2004-06-09 |
| JP2003128922A (en) | 2003-05-08 |
| DE60223832T2 (en) | 2008-10-30 |
| US20070273051A1 (en) | 2007-11-29 |
| US20040241927A1 (en) | 2004-12-02 |
| US7271232B2 (en) | 2007-09-18 |
| KR100909575B1 (en) | 2009-07-29 |
| WO2003035763A1 (en) | 2003-05-01 |
| DE60223832D1 (en) | 2008-01-10 |
| EP1442081B1 (en) | 2007-11-28 |
| JP4040858B2 (en) | 2008-01-30 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |